(1S,5R)-3-hydroxymethyl-4-methylcyclohex-3-ene-1,5-diol bis(t-butyldimethylsilyl) ether

Base Information

Chemical Name:(1S,5R)-3-hydroxymethyl-4-methylcyclohex-3-ene-1,5-diol bis(t-butyldimethylsilyl) ether
CAS No.:74055-37-1
Molecular Formula:C₂₀H₄₂O₃Si₂
Molecular Weight:386.723
Hs Code.:

Synonyms:(1S,5R)-3-hydroxymethyl-4-methylcyclohex-3-ene-1,5-diol bis(t-butyldimethylsilyl) ether

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Chemical Property of (1S,5R)-3-hydroxymethyl-4-methylcyclohex-3-ene-1,5-diol bis(t-butyldimethylsilyl) ether

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Technology Process of (1S,5R)-3-hydroxymethyl-4-methylcyclohex-3-ene-1,5-diol bis(t-butyldimethylsilyl) ether

There total 10 articles about (1S,5R)-3-hydroxymethyl-4-methylcyclohex-3-ene-1,5-diol bis(t-butyldimethylsilyl) ether which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 101906-44-9
Thiocarbonic acid O-[(1S,2R,6R)-2,6-bis-(tert-butyl-dimethyl-silanyloxy)-4-hydroxymethyl-3-methyl-cyclohex-3-enyl] ester O-phenyl ester

: 74055-37-1
(1S,5R)-3-hydroxymethyl-4-methylcyclohex-3-ene-1,5-diol bis(t-butyldimethylsilyl) ether

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 100 ℃; for 3h;
DOI:10.1016/S0040-4039(00)94991-8

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 74055-37-1
(1S,5R)-3-hydroxymethyl-4-methylcyclohex-3-ene-1,5-diol bis(t-butyldimethylsilyl) ether

Guidance literature:: Multi-step reaction with 2 steps

1: imidazole / dimethylformamide / 36 h / Ambient temperature

2: LiAlH₄ / diethyl ether / 2 h / Heating

With 1H-imidazole; lithium aluminium tetrahydride; In diethyl ether; N,N-dimethyl-formamide;

Reference yield:

: 40983-58-2
methyl shikimate

: 74055-37-1
(1S,5R)-3-hydroxymethyl-4-methylcyclohex-3-ene-1,5-diol bis(t-butyldimethylsilyl) ether

Guidance literature:: Multi-step reaction with 5 steps

1: 82 percent / Et₃N, DMAP / dimethylformamide / 4 h / 0 °C

2: 75 percent / DMAP / acetonitrile / 6 h / 20 °C

3: 1.) Et₂O, 20 deg C, 12h, 2.) 125 deg C, DMSO, 4h

4: 90 percent / DIBA-H / toluene / 2 h / -78 - -30 °C

5: nBu₃SnH, AIBN / toluene / 3 h / 100 °C

With dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; diisobutylaluminium hydride; triethylamine; In N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/S0040-4039(00)94991-8